The Compound and Friends — Eric Jackson and the Search for the Next 100 Bagger

Episode Date: November 7, 2025
Guests: Downtown Josh Brown (Host, A), Michael Batnick (Co-host, B), Eric Jackson (Guest, C)

Overview

In this invigorating episode, Josh Brown and Michael Batnick sit down with Eric Jackson—founder of EMJ Capital and the face behind the “Open Army”—to discuss his wild success picking high-conviction turnaround stocks, the dynamics of meme investing, the psychology of 100x (100-bagger) bets, and the changing culture of capital markets. Eric reflects on personal lows, career resurrection through monster stock picks like Carvana and Opendoor, and the power of grassroots retail investor movements. The trio also dissect the chaotic state of AI investing with a spotlight on OpenAI’s surreal narrative, before rapid-firing through Eric’s current favorite “potential 100-bagger” picks.

Key Discussion Points & Deep Dives

1. AI Investing Mania & OpenAI’s Bizarre Moment

Timestamps: 09:00–36:30

• OpenAI's Influence While Private:

  • OpenAI is unparalleled in its influence but, unlike the big publicly traded AI firms, remains private even as it nears a trillion-dollar valuation. This secrecy frustrates investors and adds risk and opacity to the entire market.
  • “I never thought I’d see the day when a company would hit a trillion in valuation before IPOing, and yet that seems like that could literally happen.” – Eric Jackson (11:08)

• Market Implications of Private Giants:

  • The crew discusses regulatory loopholes letting massive companies with hundreds of indirect shareholders avoid going public.
  • The interconnectedness between OpenAI and giants like Microsoft, Nvidia, and Meta means that OpenAI’s behavior, finance, and leadership have an oversized impact on major public stocks.

• Sam Altman's Public Meltdowns:

  • Recent podcast appearances and social media spats (notably with Elon Musk) highlight Altman’s erratic and defensive behavior.
  • “There’s so many people that reacted to [his comments] saying, oh, this is the sign that this is the top and we’re ringing the bell... I think there is some defensiveness in him. There is some weird vibes you do pick up on.” — Eric Jackson (17:48)
  • Altman’s comments about wishing he could “burn shorts” if OpenAI were public and telling allies he could easily replace their stock are called out for their weirdness and importance.

• Risks of AI Euphoria:

  • Widespread commitments ($1.4 trillion over eight years) to OpenAI raise questions about the sector’s sustainability and the ripple risk if OpenAI stumbles.
  • Market matches previous tech cycles, but the speed of adoption (e.g., ChatGPT) dwarfs anything before—including TikTok or the iPhone.
  • Key additional risk factors: energy grid capacity, social backlash if costs are passed to consumers, and the ever-looming potential for demand to disappoint.

• Notable Quote:

  • “If you look at the CapEx, you can only conclude that the smartest people in the room believe it’s the most valuable trophy of all to capture.” – Josh Brown (29:04)
  • “I think the biggest risk is going to be that the energy grid can’t keep up with the demands.” – Eric Jackson (30:21)

2. The Art and Life-Altering Power of 100-Bagger Investing

Timestamps: 36:30–61:15

• Eric Jackson’s Journey: Boom, Bust, and Reinvention

  • Jackson relives hitting near rock-bottom after losing his fund’s major backer following a harsh drawdown, only to forge a comeback with concentrated, high-conviction bets.
  • “I had this billionaire like turn his back on me and walk away… I’ve gone through like this internal crisis and stuff. So like when people say like, oh, how do you have the gall… I just don’t care.” — Eric Jackson (61:00)

• The Carvana and Opendoor Case Studies:

  • Jackson had previously pitched Carvana and Opendoor as comeback “dead stock” picks when no one wanted them (38:00).
  • Carvana’s CEO and execs demonstrated conviction by personally making enormous buys at the low, including one CPO dropping $3.5M at $7.50/share.
  • Extreme price volatility proved the value of “buying the dip” and sticking with conviction; these stocks ultimately delivered 10x–100x returns.
  • Key insight: Massive price move potential comes from being mispriced for bankruptcy, then resetting
  • “These hundred baggers… get priced as if they’re going out of business, but when they start moving up, it’s violent, you know, especially with a lot of shorts.” — Eric Jackson (47:05)

• Grassroots, Meme, and “Open Army” Power:

  • Jackson pioneered using viral social campaigns and daily videos (e.g., in front of Drake’s house) to rally retail investors around Opendoor stock.
  • The board’s initial resistance gave way to engagement as they recognized the share-moving power of this new “army”.
  • “It’s...a new version of Gamestop. You know, it’s a retail group, but they are much smarter than what you typically...get from Wall street towards retail.” — Eric Jackson (61:51)

3. Modern Investor Culture: Embracing the Circus

Timestamps: 36:25–41:00, 57:58–61:40

• Modern Investors Love Unconventional CEOs:

  • New norms embrace wild CEO behavior—telling off Shorts, engaging in social drama—because younger investors enjoy the spectacle and identify with the underdog.
  • “They love seeing the leadership...act as unconventionally as possible, telling people to go f*** themselves if they don’t agree. It’s almost like a version of pro wrestling.” — Josh Brown (36:25)

• Social Media as Investor Community:

  • The convergence of stock research, retail speculation, and meme madness—in forums like Twitter and through figures like Jackson—reshapes what it means to be a stock “influencer”.

• Responsibility and Risk:

  • Jackson acknowledges the weight of influencing “regular people” jumping in with real money. He sees the tension between “lottery ticket” hope and genuine fundamental research—he urges caution but also sees himself as a role model for positive engagement.

4. Rapid-Fire Lightning Round: Eric’s Current 100-Bagger Plays

Timestamps: 69:14–81:18

• Philosophy: Only stocks that could theoretically 100x enter his portfolio.

  • “Nothing goes into my portfolio that I don’t feel has that possibility...could be four years, could be five years.” — Eric Jackson (69:14)

• Highlighted Current Bets:

  • Opendoor (OPEN): Reviewer favorite; thesis based on morphing into mortgage/title, short squeeze potential, and retail mobilization.
  • Better.com (BETR): Mortgage originator, leverages AI to eliminate thousands of manual jobs—famous for viral CEO firing Zoom clip.
    • “I think this is going to be the poster child for why AI is not a bubble.” — Eric Jackson (69:58)
  • Iron (IRN) & Cypher (CIFR): Data center and infrastructure plays.
    • Transitioned from bitcoin mining to leasing out high-demand data center capacity to AI/cloud companies.
    • “When I was buying it at nine bucks … people were saying ‘these guys are just former bitcoin miners.’” (76:12)
  • Sana Biotechnology (SANA): Potential cure for type 1 diabetes; stem cell and biotech moonshot.
    • “They...cured [patients] of type 1 diabetes.” — Jackson (77:37)
  • BTQ Technologies: “Post-quantum cryptography” (cybersecurity for the quantum age).
    • “They’re trying to be the Crowdstrike for quantum.” — Eric Jackson (79:48)
  • Defi Technologies (DEFT): Tokenizing sovereign debt and crypto-native ETFs in Europe.
  • Etha ETF (ETHA): Bullish on Ethereum through liquid ETF.

• Meta Portfolio Strategy:

  • Jackson and Brown riff on launching a tongue-in-cheek “lottery ticket ETF” for retail investors, explicitly targeting those seeking moonshot returns.
    • “My new active ETF, it’s a collection literally of lottery tickets. Get long this thing with money that, if it goes to zero, you don’t care… This is explicitly what I’m doing.” — Josh Brown (82:56)

5. Memorable Quotes & Banter

On OpenAI's Market Power:

“These companies never get profitable first. They always go at breakneck speed, right?” – Eric Jackson, (27:50)

On the Modern Investor Audience:

“The audience for these antics is 27 years old… They love this shit. It’s a spectator sport.” – Josh Brown, (36:25)

On Surviving and Bouncing Back:

“I’ve gone through so much crap...so like when people say, how do you have the gall… I just don’t care. I believe in Opendoor. I believe in the types of philosophies that I’m advocating.” – Eric Jackson, (61:00)

On Meme Stock Risks:

“If something goes wrong, you kind of become forever associated with, for better or for worse.” – Josh Brown, (60:21)

On the Lottery ETF:

“You’re going to get, you’re going to get me into merch… the more extreme version of something is the one that wins… That’s the thing that happens.” – Josh Brown (81:53)

On the Open Army’s Spirit:

“I get so many messages from people saying, you know, hey, I’m an electrician, I’m a pipe layer or whatever… spent three, four hours a night studying stocks…” – Eric Jackson (86:01)

6. Notable, Amusing, or Viral Moments

• Drake’s House Videos:
  Eric films daily videos in front of Drake’s house in Toronto as part of his “Open Army” campaign. His bodyguard (“Bucky”) becomes a fan and an investor.
  “He let me finish... he comes over and he’s like, ‘guys, what’s going on here?’ …And I whipped out Yahoo Finance… it’s called Opendoor… and we think it can 100x… ‘I’m buying this thing on Monday morning.’” – Eric Jackson, (66:23)

• Open 82 Party in Vegas:
  Listeners around the globe pledge to attend a future party in Vegas if Opendoor hits $82, with memes and AI videos already in circulation. (88:28–89:06)

Important Timestamps & Segments

• AI Investing & OpenAI’s Role: 09:00–36:30
• Eric Jackson’s Investing Resurrection: 36:30–41:00; Carvana/Opendoor details: 38:00–47:00
• Modern Meme Investor Culture: 36:25–41:00
• Open Army, Drake Videos: 63:31–68:20
• Eric’s Lightning Round Stock Picks: 69:14–81:18
• Meta/“Lottery Ticket” ETF Riff: 81:19–84:23
• Eric on the Open Army’s Middle-Class Base: 85:24–86:26
• Closing Party/Jokes on Risks: 88:11–89:49

Conclusion

This episode is a wild, energizing ride into the mind of a high-conviction, high-volatility investor in the social media age. Eric Jackson’s blend of personal resilience and market insight, coupled with the hosts’ honest skepticism and sharp wit, make for an essential listen on how investing has changed—and may never be the same again.

Summary prepared by your podcast summarizer — the whole story, no hype missed.